Abstract
The development of multiple-component cross-coupling reactions is a challenge due to issues of selectivity and efficiency. In the present study, we report a chromium-catalysed, multicomponent cross-coupling reaction for the synthesis of tertiary hydrocarbons using two distinct electrophiles and one nucleophile. The tertiary alkane reaction products are important three-dimensional space structures and prevalent in a variety of drugs and bioactive molecules. The strategy comprises two cross-coupling processes of inactivated geminal C–O and C–H bonds with arylmagnesium reagents and several electrophiles, enabling the inhibition of competitive side couplings to achieve high selectivity and diversification by chromium catalysis. The synthetic scope of the multicomponent process was demonstrated through the selective synthesis of a range of diarylated tertiary silanes and difluoroallylated and alkylated alkanes. The process was also found to be readily scalable and could be applied to the synthesis of market-selling drugs, anticancer agents and bioactive molecules. Mechanistic studies revealed an amphipathic diheterometalloalkane intermediate by incorporating two distinct functional groups in the formation of tertiary hydrocarbons.
